Three single men look for love in Chicago with help from a female life coach. The trio have been friends since childhood and all have different problems with women. Tim's girlfriends always dump him; Doug can't get over his ex-wife; and Kyle is a Casanova-type who fears no one really wants him. Tim gets no help from his dad, Tug, an ex-NFLer, but his si (more…)Three single men look for love in Chicago with help from a female life coach. The trio have been friends since childhood and all have different problems with women. Tim's girlfriends always dump him; Doug can't get over his ex-wife; and Kyle is a Casanova-type who fears no one really wants him. Tim gets no help from his dad, Tug, an ex-NFLer, but his sister Molly advises him to seek advice from Dr. Victoria Stangel, a famous---and gorgeous---life coach.

Season 1 Episode Guide

In the first-season finale, Dr. Stangel tells the guys to think less about themselves, so Tim volunteers at a hunger-relief center and Doug tutors a boy in math. But Kyle's idea of charity is dating an overweight woman.

Tim hopes he can pick up where he left off with a high-school sweetheart who is just as he remembers, but things are not as they seem. Meanwhile, Doug learns that Kyle is fantasizing about Dr. Stangel and blurts out that information during a session, causing Kyle to quit.

Dr. Stangel advises the men to listen to what women say, but they only get it half right: Tim hears about Molly's car trouble, but tries to help anyway after she tells him not to get involved; Doug listens to his ex-wife's claim that she has moved on, but he still thinks they can reunite; and Kyle listens to a date just long enough to hear she has a friend with “supermodel looks,” so he dumps her to find the other woman.

Tim's new girlfriend puts an aggressive spin on their relationship, so he brings her to Dr. Stangel. Meanwhile, Doug finally moves on with another woman, and Kyle attempts to shed his reputation as an easy date.

Tim finds himself in a new situation---he has to break up with a girl, but he can't find the right way or time to do it. Meanwhile, Kyle tries to help Doug move on from his divorce by setting him up with a willing partner.

Tim is dumped yet again, and his sister suggests he visit a life coach for advice on dating. His friends Doug and Kyle decide to join his sessions to get help with their own problems: Doug is fixated on his ex-wife and Kyle has a reputation as a ladies' man and cannot find a committed relationship.

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